In 1927, while working as a drag/burlesque entertainer in Paris, he married a woman said to be French royalty. They divorced two years later, but had one daughter, named Solange.

Openly gay[1] at a time when it was daring (and even dangerous) to be so, he was well known for his flamboyant lifestyle, his outrageous sense of humor, and his penchant for perfume and costume jewelry. He performed in Shakespearean plays in England before moving to San Francisco in the late 1920s. He also frequently performed in drag.

In the 1940s, male-to-female sex change operations were becoming more widely available in Europe, and Breckinridge expressed many times his desire to undergo the procedure. With the nationwide attention given to Christine Jorgensen's sex change in 1952, Breckinridge became more determined than ever to become a woman. In 1954, he announced plans to travel to Denmark and undergo the operation so he could marry his male secretary.[1] Though Breckinridge was by this time a grandfather, his granddaughter supported him in his efforts. Shortly thereafter, a San Francisco judge scuttled his Denmark trip by ordering him into court for failing to make good on an earlier agreement to pay $8,500 a year to support his elderly, blind mother in England. He then made arrangements with a sex-change surgeon in Mexico, but had a serious car accident while traveling there. He gave up his pursuit of the matter afterwards.

In 1955, he was arrested in a San Francisco waterfront bar and charged with vagrancy and jailed, though the charges were later dropped because of his family and wealth.

In 1958, Breckinridge agreed to play the role of an alien leader in the film Graverobbers from Outer Space (later retitled Plan 9 from Outer Space), directed by his friend, Ed Wood. Wood and Breckinridge were introduced to one another by their mutual friend Paul Marco, who played Kelton the Cop in three Wood films.

Breckinridge and Marco were living together in the latter's modest home at the time, despite the fact that he was a struggling B-movie actor and Breckinridge was an independently wealthy socialite. David Demering, who played the airplane co-pilot in the film, also lived with them.

Breckinridge's previous stage experience convinced Wood to cast him as the alien ruler who oversees an attempt to take over the Earth using an army of reanimated corpses. Indeed, his background made him one of the few truly experienced actors in the entire cast. Dressed in a pajama-like outfit which is curiously less ornate than those worn by his underlings, he sports very visible mascara and lipstick, and constantly rolls his eyes and mugs for the camera.

In 1959, shortly after Plan 9 From Outer Space '​s disappointing release, Breckinridge was convicted on ten counts of "sex perversion" for taking two underage boys on an excursion to Las Vegas. He was committed to the Atascadero State Hospital for the criminally insane, and released the following year.[2]

Upon his release, he returned to his San Francisco home, a Spanish style bungalow adorned with gold framed photographs of the many celebrities he met and befriended, including Princess Margaret, Noël Coward, J. Edgar Hoover, Elvis Presley, and Ed Sullivan. Breckinridge frequently opened his home to members of the growing hippie movement, who were enthralled not only by his stories of his flamboyant youth, but also his favorable opinions on free love and his encyclopedic knowledge of both gay history and the lives of closeted Hollywood stars.

In 1994, Breckinridge was surprised to find himself portrayed as a character in a major motion picture, played by Bill Murray in Tim Burton's 1994 biopicEd Wood. His advanced years and failing health, however, prevented him from participating in any of the publicity surrounding the film.

Breckinridge maintained homes on each coast – one in New Jersey and one in San Francisco.

^ abMeyerowitz, Joanne Jay (2002), How Sex Changed: A History of Transsexuality in the United States, Harvard University Press, p. 84, ISBN0-674-01379-4

^ ab"John `Bunny' Breckinridge". November 6, 1996. Retrieved 2014-12-27. John 'Bunny' Breckinridge, an eccentric and troubled San Francisco millionaire who entertained grandly, served time in jail for vagrancy and was sued by his mother for lack of support, died Tuesday, November 5th, 1996 of heart failure in a Monterey nursing home. He was 94. ...